When Jimmy returns to work, he hires Sabrina's cousin Shelley - a/k/a "Dead Tooth" - to babysit Hope. Meanwhile, Burt tries to get Virginia to quit smoking.

Sabrina's boyfriend can't make it to the deli guy's Halloween party, so Jimmy offers to put on his costume and go in his place. Virginia takes Maw Maw, who is dressed as a cat, trick-or-treating while Burt plots ways to play tricks on Jimmy.

Jimmy hopes gullible Sabrina's boyfriend Wyatt may be cheating on her in college, so he insists to go with her to Wyatt's frat's wild costume party, but conclusive evidence is perilously hard to find. In order to have contact with generation peers, Maw Maw goes to Dead Tooth's daycare. She falls for a man who also lives in the past, but that includes an affair with another crone, supposedly from his Korean War days.

A thirteen-year-old kid makes a run for Sabrina, which drives Jimmy absolutely crazy. Meanwhile, Maw Maw swallows her gold tooth and Burt and Virginia contemplate retrieving it.

Burt's annual tax return frenzy leads to a sneer about 'mere' cleaners making Virginia meanly blow all his stacked firm finances documentation into a mess. Desperate, he turns to Barney, who suggests hiring a manager and hesitantly accepts the job. Barney hires two eccentric Asian acrobats, who demonstrate the bliss and frustration of not being the boss anymore. Stil vexed, Virginia seeks an independent career of her own and chooses as example the tarot reader Sabrina and her fiancé Wyatt turn to. As their questions concern a move to Africa, Jimmy is desperate to get his rival overseas, not his beloved, and expects madame ma to pull that off. However her arrogant advice has more impact then she ever guessed or cares to take responsibility for.

Bored and increasingly desperate for a distraction even they can afford, Burt and Virginia try out various hobbies, until they agree improvisation acting fits them scoundrels. When Jimmy feels Sabrina a lost cause after her engagement with Wyatt, they also advise making her jealous of an imaginary perfect girl. Jimmy fails to wriggle out of a double date, so he needs to hire Mary-Louise from the acting class to play one. That proves harder but also more rewarding then expected.

The chance family competes in a 1K walk.

Virginia and Burt fear that Jimmy and Sabrina's marriage has lost its spark. So they use their own relationship experiences to try and shake things up.